Acrolein → 1-Formyl-4-(4,8-dimethyl-3,7-nonadienyl)-cyclohex-4-ene

HRID 464052Notes

Reaction equation

[CH3:1][CH2:2][C:3]([CH2:5][CH2:6]/[CH:7]=[C:8](/[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])\[CH3:9])=[CH2:4].[CH:16]([CH:18]=[CH2:19])=[O:17]>>[CH:16]([CH:18]1[CH2:19][CH:4]=[C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:14])[CH3:15])[CH2:2][CH2:1]1)=[O:17]

Participants

Reactant 2

HCID 7847Acrolein

HCID 15228937beta Farnesene2×

Product 1

HCID 538464021-Formyl-4-(4,8-dimethyl-3,7-nonadienyl)-cyclohex-4-eneYield 50%

Conditions

Temperature: 100 °C

Procedure

The (E)-β-farnesene-containing product of Example 1 (5.0 g) and acrolein (3.0 g) are heated together at 100° C. for two hours. The mixture is then distilled under reduced pressure to give 1-formyl-4-(4,8-dimethyl-3,7-nonadienyl)-cyclohex-4-ene as a yellow oil (2.2 g, 50%); b.p. 140°-150°/0.5τ; nD20 1.5033; M+ (m/z as % base peak): 260 (3.6); δ (CCl4) 1.70 (M, 9H), 1.90-2.30 (m, 15H), 5.16 (m, 2H), 5.50 (br, t, 1H), 9.84 (br, s, 1H).

Workup

distillationThe mixture is then distilled under reduced pressure

Sources & evidence

ORD record: ord-43a7ac704e934c00b1f7efef5f4aadab
Source dataset: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04546110

Reaction notes

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